Head of People

| Chicago
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The Why

At Topstep, individuals fully own their roles and are charged with meaningfully driving results. We work fast and continuously optimize our products to reach more and more traders worldwide.

We are looking for a Head of People to join our leadership team, acting as a strategic and tactical business partner, providing counsel, and developing vision and roadmaps on all people, L&D, and culture related initiatives. This role is a great opportunity to join an existing, motivated, high-performing team, with lots of ideas and institutional knowledge, and build it into a cohesive department. This may seem like an ambitious hire for a 60-person company, but we believe our people are a strategic asset and our competitive differentiator. We know that if we devote resources and focus to this department now, the company, including our incredible team, will be better served in the short term and the long term.

We’re looking for an inclusive leader who thinks creatively, values emotional intelligence, and strives for constant improvement of their own self and others. This role will report directly to our COO, and has the potential to grow into our first Chief People Officer.

The successful candidate will also have a genuine enthusiasm for entrepreneurship and be able to excel in a fast-paced, high energy start-up environment. 

Excited about this opportunity? Read on, keeping in mind that we strongly encourage candidates of all different backgrounds and identities to apply. Each new hire is an opportunity for us to bring in a different perspective, and we are always eager to further diversify our company. Topstep believes that diverse people and ideas result in better business, and we are committed to fostering an inclusive culture where you can thrive.

The Role, along with everything you’d expect

  • You will be joining a talented and motivated team of two who are ready to collaborate with an experienced leader to make Topstep an even better place to work
  • The role is also a great fit for candidates who have found their sweet spot in helping organizations scale both their headcount and culture, in order to achieve business goals
  • You’ll be charged with building out the People Department formally, and setting the vision and strategy for everything from employee engagement to diversity and inclusion
  • The Head of People will be the first true People Department advocate and representative on the Leadership Team and will work closely with other department heads as well as executives
  • We hope that you want to be a thought leader within our company and the industry
  • You will be asked to lead and manage the People team according to our company values. This includes monthly one-on-one meetings, mentorship, professional development goals, and overall performance toward achieving business goals

The Ideal Candidate

  • First and foremost, a people-first approach. You share the mindset that people are the most important assets a company can have, and therefore the People Department is a strategic business asset. You will have a seat at the decision-making table and contribute strategically.
  • 10-15+ years of experience in the HR/People field, with significant experience in each of recruiting, learning & development, HR, and DEI. We believe in the well-being of our team and this role, along with all members of the team, will model how we live that.
  • 3-5+ years as a senior people leader, recruiting, leading, and developing a high-performing team, as well as experience in strategic planning and implementation 
  • Knowledge of Organizational Behavior as it relates to HR/People. It is imperative to understand our people and our culture, to ensure that we have the right people to enable growth. This role is not here solely to ensure compliance and risk management.
  • Leadership of strategic thinkers, peers, and the strategic direction of the organization. We need someone who can create a vision - both organization-wide and for the department
  • Change Management experience. You’ve successfully guided an organization or department through significant organizational change; we lose sleep over scaling our culture, especially in our new “Work from Anywhere” environment!
  • Experience with and passion for Diversity and Inclusion initiatives, including guiding toward a company vision, managing a budget, and influencing important decisions
  • Ready to lead our employee retention strategy, through learning and development, compensation philosophy, innovative benefits, and career laddering
  • Ability to remain high level. We know it’s hard because this work is really fun, but we need someone who can truly stay out of the weeds to ensure that we are always progressing toward a more ambitious goal!
  • Experience within a start-up environment preferred. We are a growth-stage company, but we run lean and move fast. As such, you will play a key role in guiding how to best leverage our resources and energy.
  • Willing and eager to play an active role in recruiting a diverse team. We believe diverse people and ideas result in better business, and look to our leaders to help with our diversity efforts

Topstep Benefits

  • Competitive salary and bonus incentives 
  • 401(k) plus match, to help plan for your future
  • Generous paid family leave, plus flexible ramp up period upon return, and extra PTO days
  • Access to senior management and mentoring opportunities
  • Monthly team Innovation Labs, which contribute to long term strategic decisions
  • Vacation bonus, when you take off 5 consecutive days to fully clock out
  • #TopstepTravel, a semi-regular raffle for luxury accommodations in a variety of cities
  • Professional development budget, provided for continuing education, training, and workshops
  • Work from Anywhere policy, to respond to an ever-changing work climate
  • Flexible Schedule Options, including 4-day workweek and half day Friday schedules
  • Employee Assistance Program, for when you need some professional support in your personal life
  • Coming [back] Soon: Company parties and outings, happy hours and catered lunches, breakfast and snack bar
  • Coming [back] Soon: Annual company-wide Step Up Day, a day spent giving back to our community
  • Graceful Leave Policy
  • Casual work environment and dress code
  • Summer Friday (flexible) hours 
  • Opportunities to work from home
  • Pre-tax spending accounts, for your dependent and health care needs plus transportation
  • Paid time off (starting at 15 days, increasing annually), plus paid holidays, paid sick days, and paid volunteer hours
  • Medical, dental, vision, life, long-term and short-term disability insurance 


Is Topstep the place for you? If so, apply today! We look forward to hearing from you.

TopstepTrader is an Equal Opportunity Employer and does not discriminate against any employee or applicant on the basis of race, gender, age, disability, or any other basis protected under the law.

Please submit your professional resume, and more importantly a cover letter highlighting your relevant experience and how you will approach this role. Because we want to read each and every application, please be sure your cover letter is specific, personal, and under one page in length. Thank you!

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Location

We are eager to get back to our warm, welcoming office in the West Loop, with plenty of snacks, friendly faces, and sometimes adorable dogs, too!

An Insider's view of Topstep

What's something quirky about your company?

We have some quirky debates that people are really passionate about. Cinnamon in coffee and the Oxford comma are two long-running ones that get heated. Our most recent debate was whether or not a hotdog is a sandwich! We spent a whole lunch hour debating, and the best part was that, no matter your opinion, you had a chance to make yourself heard.

Nick

Customer Support Rep

What kinds of technical challenges do you and your team face?

We have an exciting challenge to parallelize how we collect and process trading data. It's important for each user to know their account performance before the next trading day, which is less than 2 hours after trading close. Updating, collecting, and evaluating to be more efficient will enable us to take on more users and trading platforms.

Matt

Software Developer

How has your career grown since starting at the company?

At Topstep, I was encouraged to pursue my interests and not just ‘stay in my lane’. As a support rep, I had the unique opportunity to learn everything about our product and users while familiarizing myself with our tech stack in my free time. Now, as a business analyst, I get to combine these skills and help the company decide what to build next.

Phil

Business Analyst

What unique initiatives do you have that encourage innovation?

An exciting aspect about working at TopstepTrader is our commitment to Innovation. The company conducts a monthly Innovation Lab and my team (Marketing) has a weekly Innovation Hour-either meeting together to take advantage of group think or it’s self-directed. We continue to outpace the industry as the concept is so ingrained in our belief system!

Robin

VP of Marketing

How would you describe the company’s work-life balance?

As someone who recently had her first child, I can only describe TST’s work-life balance as fantastic and flexible! I know exactly what is expected of me, so if an emergency comes up and I need to leave to take care of my child, or spend some extra time with him, I’m met with encouragement and understanding instead of opposition or guilt.

Anne

HR Manager

What are Topstep Perks + Benefits

Topstep Benefits Overview

We believe in the well-being of our team, so we always look for more ways to reflect that in our benefits package, and company perks. Along with expected health and life insurance coverage, we offer a generous paid family leave, 401(k) match of 5%, 8 paid volunteer hours, a professional development budget for each team member, and our leadership team is extremely accessible. Not only that, but we’re ahead of the game when it comes to an inclusive environment for our diverse team, as well as an innovative culture (hint: they’re two of our 6 stated company values, and we live them).

Culture
Volunteer in local community
Friends outside of work
Eat lunch together
Intracompany committees
Daily stand up
Open door policy
Team owned deliverables
Team based strategic planning
Group brainstorming sessions
Pair programming
Open office floor plan
Diversity
Unconscious bias training
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability Insurance
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Wellness Programs
Team workouts
Acme Co.'s team fitness initiatives include In-office yoga, Sponsored race teams.
Retirement & Stock Options Benefits
401(K)
401(K) Matching
Topstep's 401(k) retirement plan matches 100% of an employee's contributions up to 4%.
Performance Bonus
We have an Employee of the Month - who we call our Topstepper - awarded for performance while living our values, plus we have a discretionary performance bonus which is distributed twice annually.
Child Care & Parental Leave Benefits
Generous Parental Leave
At one year of service: Up to 13 weeks paid leave for primary caregiver + four weeks paid leave for the secondary caregiver + extra PTO days for both + flexible ramp up period upon return!
Flexible Work Schedule
Topstep offers a flexible schedule for most roles and is also very collaborative. We offer Summer Fridays, work from home, and are generally flexible to support your life.
Return-to-work program post parental leave
Vacation & Time Off Benefits
Generous PTO
Paid time off - starting at 15 days and increasing annually - plus paid holidays, sick days, and floating holidays. The best is a $500 bonus for taking 5 consecutive PTO days!
Paid Volunteer Time
We believe that Giving Back Moves Us All Forward (one of our 6 values), so we offer each team member 8 VPTO hours to use as they wish. We also volunteer as an entire company one day each year!
Paid Holidays
Paid Sick Days
Perks & Discounts
Beer on Tap
Casual Dress
We trust all team members to Dress For Your Day so, get as casual as you like! Slippers are a must-have during the winter.
Commuter Benefits
Company Outings
Monthly FUNCtions and dept outings, killer annual holiday parties, celebrations galore, Step Up Day, new hire happy hours, and the list goes on.
Stocked Kitchen
Topstep has a fully stocked kitchen including unlimited snacks, Starbucks coffee, Tiesta Tea and all of the Starburst and M&Ms you can handle.
Some Meals Provided
Happy Hours
Recreational Clubs
Some recent examples are: 12" softball league, bocce ball, and shuffleboard at Royal Palms. We're always open to new ideas so, start something!
Professional Development Benefits
Job Training & Conferences
In addition to career coach access and quarterly team learning events, we also offer each team member a professional development budget to use as they wish.
Diversity Program
We started our D&I Committee in March '17 and today have six sub-committees to focus on hiring practices, training, cultural days of awareness and celebration, and major events, like Int'l Women's Day
Lunch and learns
Cross functional training encouraged
Promote from within
Time allotted for learning
Online course subscriptions available
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